CN113861321A - Synthesis method of 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid - Google Patents
Synthesis method of 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid Download PDFInfo
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- CN113861321A CN113861321A CN202111126998.6A CN202111126998A CN113861321A CN 113861321 A CN113861321 A CN 113861321A CN 202111126998 A CN202111126998 A CN 202111126998A CN 113861321 A CN113861321 A CN 113861321A
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Abstract
The invention relates to a synthesis method of 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid. The method comprises the steps of taking N-vinyl imidazole and alkyl bromide compounds as raw materials, firstly reacting under a high-pressure protective atmosphere to obtain an intermediate 1-vinyl-3-alkyl imidazole bromide, then carrying out ion exchange on the intermediate, reacting with glycine in absolute ethyl alcohol to obtain 1-vinyl-3-alkyl imidazole glycinate ionic liquid, and finally obtaining the 1-vinyl-3-alkyl imidazole glycinate polymeric ionic liquid with high purity through Azodiisobutyronitrile (AIBN) initiated polymerization reaction. The method provided by the invention overcomes the problem of halogen salt impurities in the existing three-step method, the whole reaction process does not generate solid wastes, and the method has the advantages of simple synthesis steps, strong operability, environmental friendliness, high product yield and the like.
Description
Technical Field
The invention relates to the technical field of polymeric ionic liquid, in particular to a brand new synthesis method of 1-vinyl-3-alkyl imidazole glycinate polymeric ionic liquid.
Background
The ionic liquid is a green organic compound with a structure and a function which can be designed. Due to the special physicochemical property and the advantages of difficult volatilization, wide liquid range and wide electrochemical window and the like, the application and research of the ionic liquid in the aspects of separation, catalysis, organic synthesis, electrochemistry and the like have made a lot of progress, and the ionic liquid is considered to be a novel environment-friendly green medium with wide application prospect in green synthesis and clean production. The polymerized ionic liquid is a kind of ionic liquid polymer which is generated by polymerizing ionic liquid monomers and has anionic and cationic groups on a repeating unit, and has the excellent performances of both the ionic liquid and the polymer.
Imidazole ionic liquid is the most common type of ionic liquid, and is widely used for organic solvents, lubricants, adhesives, other auxiliaries and the like due to the advantages of low toxicity, low price and the like. The 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid is a typical imidazole polymerized ionic liquid, and the conventional synthesis method is a three-step method: firstly, uniformly mixing N-vinyl imidazole and a chloroalkyl or alkyl bromide compound according to a certain proportion, adding solvents such as ethyl acetate and the like, carrying out heat preservation reaction on the obtained mixture in a reactor at the temperature of 60-80 ℃ for a period of time, then layering, removing the solvent phase, and concentrating to obtain an intermediate 1-vinyl-3-alkyl imidazole chloride salt [ ARmim ] [ Cl ] or 1-vinyl-3-alkyl imidazole bromide salt [ ARmim ] [ Br ]; dissolving corresponding salt (such as glycine) with solvent such as ethanol, mixing with intermediate [ ARmim ] [ Cl ] or [ ARmim ] [ Br ], stirring uniformly for ion exchange, filtering off halide salt generated by reaction, and concentrating the collected filtrate to obtain pure ionic liquid [ ARmim ] [ Gly ]; and finally, mixing the [ ARmim ] [ Gly ] pure product with AIBN to initiate polymerization reaction, and finally obtaining the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid. For literature see CN105482327A, CN101665462A, etc.
As can be seen from the analysis, the existing three-step process generally has the following problems: the whole synthesis process generates a large amount of halogen salt impurities, the main components of which are residual and unreacted N-vinyl imidazole, alkyl bromide compounds and some reaction byproducts, including bromine-vinyl imidazole, N-butyl imidazole bromine and the like. These halogen salt impurities are relatively complex to handle and costly, which is not conducive to successful industrial production. Therefore, how to improve the production process of the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid and develop an industrial polymerized ionic liquid synthesis method for avoiding the generation of halogen salt impurities is a problem which is urgently needed to be solved at present.
Disclosure of Invention
The invention aims to provide a synthesis method of a novel 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid, which comprises the following steps: (a) under the high-pressure protective atmosphere, mixing and heating N-vinyl imidazole and alkyl bromide for reaction to obtain an intermediate product A [ ARmim ] [ Br ]; (b) dissolving the intermediate product A in water, treating the obtained solution with anion exchange resin, and completely removing bromide ions to obtain an intermediate product B [ ARmim ] [ OH ]; (c) mixing glycine, the intermediate product B and an alcohol solvent for reaction, and separating and purifying to obtain 1-vinyl-3-alkyl imidazole glycinate ionic liquid [ ARmim ] [ Gly ]; (d) mixing [ ARmim ] [ Gly ] with AIBN and alcohol solvent, and carrying out polymerization reaction to obtain the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid.
Further, the high-pressure protective atmosphere in the step (a) is specifically nitrogen or argon, the pressure of the protective atmosphere before reaction is 0.1-0.5MPa, and the alkyl bromide compound is specifically n-butyl bromide. The high pressure inert reaction atmosphere is selected because in the reaction process of the N-vinyl imidazole and the alkyl bromide compound, the reaction is difficult to continue when the main raw material N-vinyl imidazole is little remained, and the alkyl bromide compound is difficult to form a free state under the conventional conditions and further interact with nitrogen atoms on the imidazole. After the inert gas is filled and a certain pressure is applied, the reaction can be promoted to continue and smoothly proceed and be completely reacted, the conversion rate and the reaction efficiency are improved, and the problems of impurity residue and post-treatment are avoided.
Further, the reaction temperature in the step (a) is controlled to be 60-80 ℃, the reaction time is within 24h, and the stirring speed of 100-400r/min is kept in the reaction process.
Further, after the reaction in the step (a) is finished, the mixture is repeatedly washed by ethyl acetate for multiple times (2-3 times), and after liquid separation, the lower layer liquid is concentrated in vacuum to obtain an intermediate product A. The ethyl acetate washing can remove a small amount of unreacted alkyl bromide in the product, and the vacuum concentration can further remove residual low-boiling impurities, which is helpful for improving the purity of the final product.
Further, in the step (c), the reactor is preheated to 20-30 ℃, glycine and the intermediate product B are added to react for 12-24h at the temperature of 20-30 ℃ under the condition of heat preservation and stirring, and the stirring speed is 500 r/min; after the reaction is finished, rotary evaporation is carried out to remove water, and then absolute ethyl alcohol is added to continue stirring and reacting for 12-24h under the same conditions.
Further, the alcohol solvent used in steps (c) to (d) is absolute ethanol. The intermediate product B generated by the reaction has poor fluidity (is viscous) and is difficult to be uniformly mixed with raw materials such as glycine, so that the pressure reaction container needs to be preheated to a proper temperature in advance and then is added with the raw materials for mixing, so as to improve the fluidity and the mixing uniformity of the raw materials.
Further, the reaction of step (c) was completed and filtered, and the obtained filtrate was concentrated in vacuo to remove the solvent.
Further, the polymerization reaction time in the step (d) is 3-12h, and the reaction is promoted by irradiating the mixture with a deuterium lamp (300W) during the polymerization.
Further, the molar ratio of the N-vinyl imidazole to the alkyl bromide compound in the step (a) is 1.0-1.5, the molar ratio of the intermediate product B to the glycine in the step (c) is 0.5-1.5, the molar ratio of the intermediate product B to the alcohol solvent is 1:3-3.5, and the addition amount of AIBN in the step (d) is 5-15% of the molar amount of the N-vinyl imidazole.
Compared with the prior art, the beneficial effects of the invention are embodied in the following aspects:
(1) the synthesis atmosphere of [ ARmim ] [ Br ] is optimized and improved, the reaction is promoted to the end by using high-pressure inert gas, the utilization rate of raw materials is improved as much as possible, the residue of the raw materials in intermediate products is reduced to the maximum extent, and the processing pressure of separation and purification and impurities is reduced;
(2) the halogen in the [ ARmim ] [ Br ] is replaced in advance by using the ion exchange resin, so that halogen salt impurities are prevented from being formed in the subsequent reaction process, and side reactions in the [ ARmim ] [ Gly ] synthesis process are also prevented from occurring;
(3) the use of the preheating reactor and absolute ethyl alcohol ensures that [ ARmim ] [ OH ] and glycine are fully and uniformly mixed, and is beneficial to improving the reaction degree of the [ ARmim ] [ OH ] and the glycine and the product yield;
(4) the method has the advantages of simple process, environmental protection, renewable and recyclable solvent, no side reaction, high product yield, good quality and the like, does not generate solid waste in the whole synthesis process, and is favorable for low-cost industrial production.
Detailed Description
In order to make those skilled in the art fully understand the technical solutions and advantages of the present invention, the following embodiments are further described.
Comparative example 1
94.11g of 94.11g N-vinylimidazole and 35.56g of n-butyl bromide (molar ratio of 1:1) were put into a three-necked flask and refluxed with stirring to effect a reaction. The stirring speed is 300r/min, the reaction temperature is controlled at 60 ℃, and the reaction time is 12 h. After the reaction is finished, an intermediate mixture is obtained, ethyl acetate is used for washing for 2-3 times, the upper layer liquid with residual N-butyl bromide and N-vinyl imidazole is removed after layering, the separated lower layer liquid is concentrated in vacuum, 87.21g of intermediate [ ARmim ] [ Br ] is finally obtained, and the yield is 67%.
And then dissolving all prepared intermediates [ ARmim ] [ Br ] in water, and directly mixing and reacting with glycine at the stirring speed of 500r/min at the reaction temperature of 20 ℃ for 12 h. After the reaction is finished, performing rotary evaporation to remove water, and then adding absolute ethyl alcohol to stir for reaction. Wherein the molar ratio of the intermediate [ ARmim ] [ Br ] to the glycine and the absolute ethyl alcohol is 1:1:3, the stirring speed is 200r/min, the reaction temperature is 20 ℃, and the reaction time is 12 h. And after the reaction is finished, filtering the mixture, removing excessive unreacted glycine, concentrating the collected filtrate in vacuum, adding absolute ethyl alcohol, stirring, concentrating in vacuum for multiple times, and further purifying to obtain 72.41g of brown yellow oily transparent liquid, namely the 1-vinyl-3-alkylimidazole glycinate ionic liquid [ ARmim ] [ Gly ]. The liquid was darker in color, indicating that it contained a few by-product impurities that were not removed.
And finally, under the irradiation of a 300W deuterium lamp, taking absolute ethyl alcohol as a solvent, mixing [ ARmim ] [ Gly ] and AIBN (the using amount is 15 percent of the mol number of the N-vinyl imidazole) for polymerization reaction for 7 hours, and concentrating the obtained mixture in vacuum to obtain the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid with the yield of 56 percent.
Example 1
94.11g N-vinyl imidazole and 35.56g of n-butyl bromide (molar ratio of the two is 1:1) are added into a pressure reaction vessel, then the vessel is sealed and vacuumized to-0.08 MPa, then nitrogen is filled to adjust the pressure to 0.1MPa, and the reaction is carried out under the stirring state. The stirring speed is 300r/min, the reaction temperature is controlled at 60 ℃, and the reaction time is 12 h. After the reaction is finished, an intermediate mixture is obtained, ethyl acetate is used for washing for 2-3 times, the upper layer liquid with a small amount of residual N-butyl bromide and N-vinyl imidazole is removed after layering, the separated lower layer liquid is concentrated in vacuum, 119.30g of intermediate [ ARmim ] [ Br ] is finally obtained, and the yield is 96%. Compared with the comparative example, the yield is obviously improved.
The resulting intermediate [ ARmim ] [ Br ] was dissolved in water, and the resulting solution was thoroughly treated with an anion exchange resin to give an intermediate [ ARmim ] [ OH ].
Preheating a pressure reaction vessel to 30 ℃, and then adding all prepared intermediates [ ARmim ] [ OH ] and glycine into the reaction vessel for stirring reaction. The stirring speed is 500r/min, the reaction temperature is 20 ℃, and the reaction time is 12 h. After the reaction is finished, performing rotary evaporation to remove water, and then adding absolute ethyl alcohol to stir for reaction. Wherein the molar ratio of the intermediate [ ARmim ] [ OH ] to glycine to absolute ethyl alcohol is 1:1:3, the stirring speed is 200r/min, the reaction temperature is 20 ℃, and the reaction time is 12 h. And after the reaction is finished, filtering the mixture to remove excessive unreacted glycine, collecting filtrate, concentrating the filtrate in vacuum, adding absolute ethyl alcohol, stirring, concentrating in vacuum for multiple times, and further purifying to obtain 110.22g of oily transparent liquid, namely the 1-vinyl-3-alkylimidazole glycinate ionic liquid [ ARmim ] [ Gly ].
And finally, under the irradiation of a 300W deuterium lamp, taking absolute ethyl alcohol as a solvent, mixing [ ARmim ] [ Gly ] and AIBN (the using amount is 15 percent of the mol number of the N-vinyl imidazole) for polymerization reaction for 7 hours, and concentrating the obtained mixture in vacuum to obtain the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid with the yield of 92 percent.
Compared with a control group, the intermediate product and the final product prepared by the embodiment are very transparent, and do not appear to appear dark color or other abnormal colors because of more impurities, the purity of the final product is obviously improved, and the yield is also greatly improved.
Example 2
94.11g of 94.11g N-vinylimidazole and 53.34g of n-butyl bromide (molar ratio of 1:1.5) were charged into a pressure reaction vessel, the vessel was sealed and evacuated to-0.09 MPa, then nitrogen was introduced to adjust the pressure to 0.3MPa, and the reaction was carried out under stirring. The stirring speed is 100r/min, the reaction temperature is controlled at 80 ℃, and the reaction time is 12 h. After the reaction is finished, an intermediate mixture is obtained, the mixture is washed for 2 to 3 times by ethyl acetate, the upper layer liquid with a small amount of residual N-butyl bromide and N-vinyl imidazole is removed after layering, the separated lower layer liquid is concentrated in vacuum, 137.13g of intermediate [ ARmim ] [ Br ] is obtained, and the yield is 95%. Compared with the comparative example, the yield is obviously improved.
The [ ARmim ] [ Br ] is dissolved in water and the resulting solution is fully treated with an anion exchange resin to give an intermediate [ ARmim ] [ OH ].
Preheating a pressure reaction vessel to 40 ℃, then adding all prepared intermediates [ ARmim ] [ OH ] and glycine into the pressure reaction vessel, stirring at the speed of 300r/min, reacting at the temperature of 20 ℃ and reacting for 12 hours. After the reaction is finished, the absolute ethyl alcohol is added for stirring reaction after rotary evaporation and dehydration. Wherein the molar ratio of the intermediate [ ARmim ] [ OH ] to glycine and absolute ethyl alcohol is 1:1:3, the stirring speed is 200r/min, the reaction temperature is 30 ℃, and the reaction time is 12 h. After the reaction, the mixture was filtered to remove excess unreacted glycine, the filtrate was collected and concentrated in vacuo, and then added with anhydrous ethanol and stirred and concentrated in vacuo several times for further purification to finally obtain 126.81g of a pale yellow oily transparent liquid, i.e., [ ARmim ] [ Gly ].
And finally, under the irradiation of a 300W deuterium lamp, taking absolute ethyl alcohol as a solvent, mixing [ ARmim ] [ Gly ] and AIBN (the using amount is 5 percent of the mol number of the N-vinyl imidazole) for polymerization reaction for 6 hours, and concentrating the obtained mixture in vacuum to obtain the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid with the yield of 93 percent.
Example 3
94.11g N-vinyl imidazole and 44.45g n-butyl bromide (molar ratio of the two is 1:1.25) are added into a pressure reaction vessel, then the vessel is sealed and vacuumized to-0.09 MPa, then nitrogen is filled to adjust the pressure to 0.5MPa, and the reaction is carried out under the stirring state. The stirring speed is 400r/min, the reaction temperature is controlled at 70 ℃, and the reaction time is 12 h. After the reaction is finished, an intermediate mixture is obtained, the mixture is washed for 2-3 times by ethyl acetate, the upper layer liquid with a small amount of residual N-butyl bromide and N-vinyl imidazole is removed after layering, and the separated lower layer liquid is concentrated in vacuum to obtain 126.09g of an intermediate [ ARmim ] [ Br ], wherein the yield is 94%. Compared with the comparative example, the yield is greatly improved.
The [ ARmim ] [ Br ] is dissolved in water and the resulting solution is fully treated with an anion exchange resin to give an intermediate [ ARmim ] [ OH ].
Preheating a pressure reaction vessel to 35 ℃, then adding all prepared intermediates [ ARmim ] [ OH ] and glycine into the pressure reaction vessel, stirring at the speed of 400r/min, reacting at the temperature of 20 ℃, and reacting for 12 h. After the reaction is finished, the absolute ethyl alcohol is added for stirring reaction after rotary evaporation and dehydration. Wherein the molar ratio of the intermediate [ ARmim ] [ OH ] to glycine and absolute ethyl alcohol is 1:1:3, the stirring speed is 300r/min, the reaction temperature is 25 ℃, and the reaction time is 24 h. After the reaction, the mixture was filtered to remove excess unreacted glycine, the filtrate was collected and concentrated in vacuo, and then added with anhydrous ethanol and stirred and concentrated in vacuo several times for further purification to finally obtain 115.00g of a pale yellow oily transparent liquid, i.e., [ ARmim ] [ Gly ].
And finally, under the irradiation of a 300W deuterium lamp, taking absolute ethyl alcohol as a solvent, mixing [ ARmim ] [ Gly ] and AIBN (the using amount is 5 percent of the mol number of the N-vinyl imidazole) for polymerization for 5 hours, and concentrating the obtained mixture in vacuum to obtain the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid with the yield of 91 percent.
Claims (9)
- The synthesis method of the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid is characterized by comprising the following steps:(a) under the high-pressure protective atmosphere, mixing N-vinyl imidazole and alkyl bromide, heating and reacting to obtain an intermediate product A;(b) dissolving the intermediate product A in water, and treating the obtained solution with anion exchange resin to completely remove bromide ions to obtain an intermediate product B;(c) mixing glycine, the intermediate product B and an alcohol solvent for reaction, and separating and purifying to obtain 1-vinyl-3-alkyl imidazole glycinate ionic liquid;(d) mixing the 1-vinyl-3-alkyl imidazole glycinate ionic liquid with AIBN and an alcohol solvent, and polymerizing to obtain the 1-vinyl-3-alkyl imidazole glycinate polymerized ionic liquid.
- 2. The method of synthesis according to claim 1, characterized in that: the high-pressure protective atmosphere in the step (a) is specifically nitrogen or argon, and the pressure of the protective atmosphere before reaction is 0.1-0.5 MPa.
- 3. The method of synthesis according to claim 1, characterized in that: in the step (a), the reaction temperature is controlled to be 60-80 ℃, the reaction time is within 24h, and the stirring speed of 100-400r/min is kept in the reaction process.
- 4. The method of synthesis according to claim 1, characterized in that: and (b) repeatedly washing the reaction product in the step (a) with ethyl acetate for multiple times after the reaction is finished, and carrying out liquid separation and then carrying out vacuum concentration on the lower layer liquid to obtain an intermediate product A.
- 5. The method of synthesis according to claim 1, characterized in that: in the step (c), the reactor is preheated to 20-30 ℃, glycine and the intermediate product B are added to react for 12-24h at the temperature of 20-30 ℃ under the condition of heat preservation and stirring, and the stirring speed is 100-; after the reaction is finished, rotary evaporation is carried out to remove water, and then absolute ethyl alcohol is added to continue stirring and reacting for 12-24h under the same conditions.
- 6. The method of synthesis according to claim 1, characterized in that: filtering after the reaction in the step (c) is finished, and vacuum-concentrating the obtained filtrate to remove the solvent.
- 7. The method of synthesis according to claim 1, characterized in that: the polymerization reaction time of the step (d) is 3-12h, and the mixture is irradiated by a deuterium lamp during the polymerization process.
- 8. The method of synthesis according to claim 1, characterized in that: the alkyl bromide compound in the step (a) is n-butyl bromide, and the alcohol solvent in the steps (c) to (d) is absolute ethyl alcohol.
- 9. The method of synthesis according to claim 1, characterized in that: the molar ratio of the N-vinyl imidazole to the alkyl bromide compound in the step (a) is 1.0-1.5, the molar ratio of the intermediate product B to the glycine in the step (c) is 0.5-1.5, the molar ratio of the intermediate product B to the alcohol solvent is 1:3-3.5, and the adding amount of AIBN in the step (d) is 5-15% of the molar number of the N-vinyl imidazole.
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